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Chilmark Vacation Rentals

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Check prices for these dates

In two weeks
Sep 12 - Sep 14
In one month
Sep 26 - Sep 28
In two months
Oct 24 - Oct 26
In three months
Nov 21 - Nov 23

Vacation Rentals in Chilmark

Our top choices for Chilmark vacation rentals

Secluded Guest House overlooking Menemsha Pond. Dogs welcome + Lvl2 EV charger.
Terrace/patio

Secluded Guest House overlooking Menemsha Pond. Dogs welcome + Lvl2 EV charger.

10.0 out of 10, Exceptional, (53)
"We were in town for a wedding in Chilmark and the property was exactly what we needed!"
Secluded Guest House overlooking Menemsha Pond. Dogs welcome + Lvl2 EV charger.
The Club at New Seabury
Private beach nearby, beach bar

The Club at New Seabury

3.5 star property
9.0 out of 10, Wonderful, (327)
"Nice amenities. "
The Club at New Seabury
InnSeason Resorts Captain's Quarters
On the beach, white sand

InnSeason Resorts Captain's Quarters

3.5 star property
9.8 out of 10, Exceptional, (176)
"Just a quick weekend away. Great location for beach lovers. Also excellent retaurants "
InnSeason Resorts Captain's Quarters
Sea Mist Resort
Indoor pool, outdoor pool, sun loungers

Sea Mist Resort

3.0 star property
8.8 out of 10, Excellent, (134)
"Great resort with suites, very cosy with great amenities, close to excellent beach and shopping."
The price is ￥26,980
￥30,879 total
includes taxes & fees
Sep 15 - Sep 16
Sea Mist Resort
Beachside Village Resort
Seasonal outdoor pool

Beachside Village Resort

3.0 star property
9.2 out of 10, Wonderful, (99)
"Great location! Nice property! "
Beachside Village Resort
Coastal chic meets French Provençal in this newly renovated oceanfront home.
5 bedrooms, desk, iron/ironing board, travel crib

Coastal chic meets French Provençal in this newly renovated oceanfront home.

10.0 out of 10, Exceptional, (85)
"Great stay! "
Coastal chic meets French Provençal in this newly renovated oceanfront home.
Near Old Silver Beach Falmouth-Private entrance, private bedroom & shared bath
Beach nearby

Near Old Silver Beach Falmouth-Private entrance, private bedroom & shared bath

8.4 out of 10, Very Good, (20)
"So turn key and perfect for Month, Joy is an exceptional host and I’d recommend her place anytime"
The price is ￥13,122
￥27,828 total
includes taxes & fees
Sep 2 - Sep 3
Near Old Silver Beach Falmouth-Private entrance, private bedroom & shared bath
Southcape Resort Mashpee a Ramada by Wyndham
Exterior

Southcape Resort Mashpee a Ramada by Wyndham

3.0 star property
8.6 out of 10, Excellent, (201)
"Enjoyed our stay."
Southcape Resort Mashpee a Ramada by Wyndham
Tranquil Home with Private Deck - Walk to Beaches and Downtown Oak Bluffs
Exterior

Tranquil Home with Private Deck - Walk to Beaches and Downtown Oak Bluffs

6.2 out of 10, (24)
"The property is quiet, spacious and was within a walkable mile of downtown Oak Bluffs. The beds were comfortable. Plenty of clean linens and towels. The house could use some updating. The coffee maker, drinking glasses, and silverware need to be replaced with cleaner ones. And the torn portions of the sectional couch should be fixed. I would definitely stay at the property again."
Tranquil Home with Private Deck - Walk to Beaches and Downtown Oak Bluffs
Walking Distance From Oak Bluffs Ferry Terminal With 180 Degree Ocean View.
Interior

Walking Distance From Oak Bluffs Ferry Terminal With 180 Degree Ocean View.

9.4 out of 10, Exceptional, (84)
"Close to buses, restaurants and ferries. 10/10, we would stay again."
The price is ￥56,331
￥94,341 total
includes taxes & fees
Sep 4 - Sep 5
Walking Distance From Oak Bluffs Ferry Terminal With 180 Degree Ocean View.
Relax & Unwind this Fall, at a very private & relaxing 1 bedroom 1 bath studio
Outdoor dining

Relax & Unwind this Fall, at a very private & relaxing 1 bedroom 1 bath studio

10.0 out of 10, Exceptional, (7)
Relax & Unwind this Fall, at a very private & relaxing 1 bedroom 1 bath studio
Amazing Views!!! Sunsets!!! Larger Roof Deck!!! Historic Martha’s Vineyard Gem!!
Dining

Amazing Views!!! Sunsets!!! Larger Roof Deck!!! Historic Martha’s Vineyard Gem!!

9.6 out of 10, Exceptional, (40)
"Fantastic beach cabin in a nice location, close to Gay Head lighthouse and several beaches, including the dog-friendly Lobsterville. Good views, plenty of land, we had a good time!"
Amazing Views!!! Sunsets!!! Larger Roof Deck!!! Historic Martha’s Vineyard Gem!!
Renovated Nantucket Style 2 Bed/2 Bath Cottage, Steps to Private Beach, Market..
Beach nearby

Renovated Nantucket Style 2 Bed/2 Bath Cottage, Steps to Private Beach, Market..

8.6 out of 10, Excellent, (44)
"Great place for a summer vacation"
Renovated Nantucket Style 2 Bed/2 Bath Cottage, Steps to Private Beach, Market..
Walking to the beach. Bars and Restaurants.
Paper towels

Walking to the beach. Bars and Restaurants.

9.6 out of 10, Exceptional, (4)
"The home was very nice and in a convenient location. Ana was very helpful and quick with communications during our stay. Would highly recommend for anyone traveling to Oak Bluffs! "
Walking to the beach. Bars and Restaurants.
Maushop Village-Exceptional, 2 bedrooms, Sleeps 4, 1.5 baths, with great views.
On the beach, sun loungers, beach towels

Maushop Village-Exceptional, 2 bedrooms, Sleeps 4, 1.5 baths, with great views.

10.0 out of 10, Exceptional, (29)
"We had a great trip and look forward to staying there again. Location is the best part!"
The price is ￥29,307
￥93,209 total
includes taxes & fees
Sep 17 - Sep 18
Maushop Village-Exceptional, 2 bedrooms, Sleeps 4, 1.5 baths, with great views.
The Costal Corner - Martha's Vineyard
Microwave, oven, stovetop, dishwasher

The Costal Corner - Martha's Vineyard

2.0 star property
10.0 out of 10, Exceptional, (1)
"This property was great for our golf trip. The 3 bedrooms were exceptional "
The Costal Corner - Martha's Vineyard
Oceanview 2 Double Bed Groundfloor Suite
Outdoor dining

Oceanview 2 Double Bed Groundfloor Suite

6.0 out of 10, (2)
"Our trip was a last minute decision, and needed to stay just one night. The location, the fast response, clear instructions, cleanliness, assigned parking and pricing all came together very nicely! "
The price is ￥27,061
￥33,205 total
includes taxes & fees
Sep 25 - Sep 26
Oceanview 2 Double Bed Groundfloor Suite
Walk to Beach & Lighthouse: Oak Bluffs Studio!
Property grounds

Walk to Beach & Lighthouse: Oak Bluffs Studio!

7.4 out of 10, Good, (3)
"Very accommodating early check in and great communication "
The price is ￥24,005
￥60,372 total
includes taxes & fees
Sep 3 - Sep 4
Walk to Beach & Lighthouse: Oak Bluffs Studio!
Waterfront Home w/ Guest Cottage
Smart TV

Waterfront Home w/ Guest Cottage

10.0 out of 10, Exceptional, (2)
"Great property. Very responsive hosts. Thank you!"
Waterfront Home w/ Guest Cottage
Private cottage nestled in center of the Vineyard
Beach nearby

Private cottage nestled in center of the Vineyard

10.0 out of 10, Exceptional, (50)
"This whole experience was better than I could have imagined. The cottage was beautiful in a perfect setting. my Hosts went the extra distance. I didn't arrive until close to midnight. My hosts had left fruit, salad, yogurt and ice cream for me. Since I was unable to get a rental car this meant I had something to eat in the morning. I will definitely stay there again! "
Private cottage nestled in center of the Vineyard
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Chilmark Hotel Reviews

Find out more about Chilmark

Find out more about Chilmark

Search for holiday rentals in Chilmark on Expedia! You can easily find your home rentals, villas, holiday apartments in Chilmark using one of the methods below:

  • View our selection of featured holiday rentals in Chilmark
  • Use the map to find apartments and other holiday homes in the Chilmark neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Chilmark while they last

Look no further and take a look at our great range of rental properties in Chilmark!

Explore a world of travel with Expedia

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Frequently asked questions

Can I find vacation rentals in Chilmark?

Yes, there are vacation rentals in Chilmark near Chilmark Chocolates, or you can select a more secluded option if you're looking for extra privacy while you relax. Chilmark is known for its beaches and wineries. Make sure you have time to check out the festivals and local tours during your trip.

What are some of the best vacation rentals that Chilmark has to offer?

Tranquil Home with Private Deck - Walk to Beaches and Downtown Oak Bluffs: This vacation home rental near Chilmark offers a patio, a barbecue grill, and air-conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave.

How many vacation rentals are there in Chilmark?

Choose from 74 Expedia vacation rentals in Chilmark for a memorable vacation.

What’s there to see and do in Chilmark?

Family-friendly attractions include Chilmark Chocolates and Fulling Mill Brook Preserve, whereas Menemsha Beach and Lucy Vincent Beach are a couple of great spots to enjoy the outdoors. While here, Chilmark Town Hall and Chilmark Public Library are other places worth a visit.

What’s a vacation rental in Chilmark like?

A vacation rental is a private property where you can stay for a long or short time in Chilmark. Vacation rentals offer amenities such as laundry facilities and kitchens so you'll be comfy for your stay. If you're concerned about cleanliness, a vacation rental can offer a sense of security away from shared hotel elevators and lobbies bustling with people while still allowing you the excitement and enjoyment of travel. You'll also get more space in a vacation rental than in a hotel, which makes a vacation rental an attractive option for a family getaway.